Pyridine → alpha-Acetoxy-[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

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Reaction Steps

To a solution of 1.10 g. of α-hydroxy-[2-(β,β,β-trichloroethoxycarbonyl)aminothiazol-4-yl)acetonitrile in 1 ml. of pyridine is added 2.5 ml. of acetic anhydride under ice-cooling and the mixture is stirred for 1 hour. To the mixture is added ether and water and the organic layer is washed with aq. NaHCO3 and further water in this order. Evaporation of ether gives α-acetoxy-[2-(β,β,β-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile. 1.3 g. NMR(ppm, 100 MHz, CDCl3): 2.20(3H,s,COCH3), 5.00(2H,s, Cl3CCH2 --), 6.60(1H,s, >CHCN), 7.30(1H,s,5-H).

Provenance & Evidence